50 Years of Chuck and Blair
by E.A. Eyre
Summary: Drabbles in the first fifty years of Chuck and Blair. Enjoy.
1. Decade One

Disclaimer: Sadly, I don't own Gossip Girl. If I did it would be renamed The Fluffy Days of Chair and all would be well...

A/N: This is just something that popped into my head. If you like it leave a review and I will continue.

Year 1 

Silence. A stifled cry.

Year 2

Blair: Mamma!

Chuck: Silence

Year 3

He took a deep breath before approaching her. He didn't know why he was so nervous. "Hi, Blair. I'm Chuck Bass."

"I know."

Year 4 

He heard her crying silently from the mat beside him. He turned to face her, tapping her on the shoulder he whispered, "What's wrong Blair?"

She sniffled, turning to face him. "I had a bad dream," she confessed.

"Don't worry, I'm right here."

Year 5 

"When I grow up I'm going to marry Nate," Blair declared, surely.

_Why him?_ Chuck thought.

Year 6 

"Chuck, can we be friends?" Blair asked, innocently

"I guess so." His heart fluttered at the thought.

"Everyone says I shouldn't talk to you."

Chuck felt his body tense. "Who cares what people think?" Chuck asked, although he already knew the answer. Blair cared.

Year 7

"Hey, Blair."

Suddenly Blair reached out and smacked Chuck on the arm.

"Ouch, what was that for?"

"Did I just imagine your crummy behavior yesterday, or did it happen?"

Chuck stayed quiet; he thought it would probably be for the best. Blair's question was rather rhetorical.

"Stop being so mean to me, or we'll stop being friends, got it?"

Year 8

They sat on Blair's bed, playing _Snakes and Ladders_.

Laughing, Blair carefully rolled the dice, making sure that she would roll a three and win the game. "Ha!" she declared, moving her piece to the final square. "I won."

Chuck felt the urge to speak up about the fact that she was obviously cheating, and although she could swing that while playing against Nate or Serena, he knew her better. But he suppressed the urge, picking up the game pieces and returning them to square one. "What do you say, Waldorf, best of three?"

Year 9 

At a yearly carnival, Blair found herself sitting on a bench with none other than Chuck, Serena and Nate having run off to do God knows what. Blair sighed. This could not be more boring.

"What do you say, Blair? You, me, the teapots?"

Blair smiled. "Sure!"

Year 10

Blair was sitting quietly at her desk when a tap from behind her made her jump.

"Don't get your panties in a twist, Waldorf. I need to borrow a pen."

"Why don't you have any? We're in school!" Blair exclaimed as she dutifully extracted a pristine ballpoint pen from her bag.

Chuck grabbed the pen and quickly jotted a number down on his hand. "Thanks," he said as he returned the pen.

"What are you doing, anyways?"

Chuck motioned to the hall where a much older girl was exiting the room. "Getting a number."

"Oh," Blair replied curtly, turning back to her work. She couldn't help but question the queasy feeling that she got in her stomach upon hearing his reply.


	2. Decade Two

A/N - Sorry for the outrageously long wait. I've had this practically finished for the longest time, but I've lost almost all inspiration for it. Anyways, I've forced myself to finish this decade. I don't know when I'll update next. It all depends on my workload at school, etc. But regardless, enjoy…

Disclaimer: Sadly, I don't own anything.

Year 11 

A/N - Sorry for the outrageously long wait. I've had this practically finished for the longest time, but I've lost almost all inspiration for it. Anyways, I've forced myself to finish this decade. I don't know when I'll update next. It all depends on my workload at school, etc. But regardless, enjoy…

Disclaimer: Sadly, I don't own anything.

"I've never understood why you like this movie so much, Waldorf," Chuck whispered into Blair's ear. They were seated side-by-side on a sofa in Blair's family's penthouse. They were, along with Nate and Serena, watching _Breakfast at Tiffany's _per Blair's request.

And, also as per usual, Serena and Nate had fallen asleep somewhere around the second scene.

"It's a testament to the connection that two people can have together," Blair replied smoothly.

"Every girls dream," Chuck mocked.

Blair sighed sadly. "It is," she murmured, glancing over at Nate.

Year 12 

Chuck was hiding around a corner at school when it happened. With his head cocked to the side, touching the cool brick of the 200 year old building, he watched as Nate gallantly kneeled in front of Blair in the center of the courtyard as he asked her to be his girlfriend.

There were two feelings that rushed through Chuck as he watched Blair smile fully and gladly accept Nate's proposal, all the while looking around the yard to ensure that she had everyone's attention. The first was happiness for Blair's happiness—common enough, Blair was his friend and why couldn't he be happy for her happiness? However, the second emotion was much more troubling. Chuck could not shake the utter remorse he felt for not being Nate, kneeling on the hard, stone floor dirtying his pants. Oh, no. Chuck would have paid 100 dry cleaner bills just to take Nate's spot. But he would pay for 1000 bills to not feel that way.

Sighing, Chuck turned away from the scene and casual strolled off of the school property, deciding he had experienced more than enough education for one day.

Year 13 

Much to Blair's chagrin, Mrs. Wyatt, her eighth grade science teacher, paired her with Chuck for a project that—as Chuck put it—was _only _worth thirty percent of their grade.

As much as Blair tried to get Chuck to focus, they still somehow ended up getting no work done in the entire month they had to work. On a Sunday, the night before the project was due, Blair marched into the Palace, fury in her every step. She found Chuck lounging on his bed and proceeded to smack him across the head with a calendar.

"Do you realize the date today, Chuck? The project is due tomorrow and we are nowhere near done!" she fumed.

"Relax, Princess. I got it done and don't worry, I'm sure it will exceed your expectations," Chuck replied, smoothly. He motioned to a table at the side of his room which held the report.

Blair would never admit it, but he did a good job. I guess the 'A' said it all.

Year 14 

"Thanks for the flowers, Chuck." Blair smiled, sadly.

Chuck frowned. "He forgot your birthday, didn't he?"

Blair nodded, lifting the peonies to her nose and breathing deeply.

Year 15 

"Why do you even like Nate?" Chuck asked, regretting the words as soon as they left his mouth. "You two don't fit."

Blair scoffed. "As compared to what? You and I?" she questioned, jokingly.

Chuck turned around to hide the hurt from his face after her obvious distain towards the two of them every being together.

Year 16 

"I love you."

Year 17 

"I love you, too."

Year 18 

"What are we doing, Chuck?" Blair sighed.

Chuck smirked. "Living," he answered.

"I'm being serious! Where do you think we'll be in ten years? I mean, don't you ever think about it?"

"No," Chuck responded, reflexively. He quickly regretted his harsh tone when he saw the hurt on her face.

Year 19 

"I love you, you know that?" Chuck offered.

Blair turned towards him on the couch. "I know," she answered, quickly turning back to the meaningless television show that neither of them was really watching.

Chuck sighed. Suddenly, "I love you" didn't seem like enough anymore.

Year 20 

Chuck came home to see Blair crying on the bed. He approached her cautiously, fearing the worst. He reached out and gently placed his hand on her shoulder, wincing when she involuntarily pulled away.

"Hey, Blair," he said quietly.

"What?" she responded sharply.

"What's wrong?" he sighed.

"Nothing. Nothing at all," she whispered. The next day Chuck realized the source of Blair's mood when Nate and Serena announced their engagement at the weekly family brunch.


End file.
